Diacetone D-glucose
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 2h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 2h; | 96% |
With sodium tetrahydroborate In ethanol; water at 0℃; for 1h; | 90% |
With sodium tetrahydroborate In ethanol; water at 20℃; for 3h; stereoselective reaction; | 84% |
3-O-tetrahydropyranyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
Diacetone D-glucose
Conditions | Yield |
---|---|
With water; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In acetonitrile at 75℃; for 0.5h; | 91% |
With iodine In methanol at 20℃; for 1h; acetal cleavage; | 90% |
3-O-(4,4'-dimethoxytrityl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
Diacetone D-glucose
Conditions | Yield |
---|---|
With iodine In methanol at 20℃; for 1h; ether cleavage; | 88% |
With water; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In acetonitrile at 75℃; for 0.25h; | 85% |
Conditions | Yield |
---|---|
Stage #1: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78℃; Stage #2: With sodium tetrahydroborate In methanol at 0℃; | 85% |
Stage #1: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose With dipyridinium dichromate; acetic anhydride In dichloromethane Stage #2: With sodium tetrahydroborate In ethanol | 83% |
Stage #1: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride In dichloromethane at -65 - 20℃; Stage #2: With sodium tetrahydroborate In methanol at 0℃; for 1h; | 82% |
1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose
A
Diacetone D-glucose
B
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol | A 4.49 g B n/a |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CrO3; Ac2O; pyridine / CH2Cl2 / 1 h / 0 °C 2: 8.0 g / NaBH4 / ethanol / 0.5 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: CrO3; Ac2O; pyridine / CH2Cl2 / 2.5 h / 0 - 20 °C 2: 4.49 g / NaBH4 / methanol View Scheme | |
Multi-step reaction with 2 steps 1: 85 percent / PCC; 3 Angstroem molecular sieves; neutral alumina / CH2Cl2 / 15 h / 20 °C 2: 96 percent / NaBH4 / aq. ethanol / 2 h / 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 32 percent / ZnCl2; H3PO4 / 30 h / 20 °C 2: 85 percent / PCC; 3 Angstroem molecular sieves; neutral alumina / CH2Cl2 / 15 h / 20 °C 3: 96 percent / NaBH4 / aq. ethanol / 2 h / 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 68 percent / ZnCl2; aq. H3PO4 / 36 h / 20 °C 2: 91 percent / pyridinium dichromate; acetic anhydride / CH2Cl2 / 4 h / 75 °C 3: 90 percent / NaBH4 / ethanol; H2O / 1 h / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1: phosphoric acid; zinc(II) chloride / 36 h / Reflux 2: dipyridinium dichromate; acetic anhydride / dichloromethane / 2 h 3: sodium tetrahydroborate / ethanol / 2 h View Scheme | |
Multi-step reaction with 2 steps 1: zinc(II) chloride; phosphoric acid / acetone 2: acetic anhydride; pyridinium chlorochromate / dichloromethane View Scheme | |
Multi-step reaction with 3 steps 1: zinc(II) chloride; phosphoric acid 2: acetic anhydride; dipyridinium dichromate / dichloromethane 3: sodium tetrahydroborate / ethanol View Scheme | |
Multi-step reaction with 3 steps 1: sulfuric acid 2: chromium(VI) oxide; pyridine; acetic anhydride / dichloromethane / 0.42 h / Cooling with ice 3: sodium tetrahydroborate; ethanol / Cooling with ice View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: zinc(II) chloride / Inert atmosphere; Schlenk technique 2: chromium(VI) oxide; acetic anhydride; pyridine / Inert atmosphere; Schlenk technique 3: sodium tetrahydroborate / ethanol; water / 3 h / 0 °C / Inert atmosphere; Schlenk technique View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: oxalyl dichloride; triethylamine / dichloromethane; dimethyl sulfoxide / -78 - 20 °C 2: sodium tetrahydroborate; water / ethanol / 1 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sulfuric acid 2: oxalyl dichloride; triethylamine / dichloromethane; dimethyl sulfoxide / -78 - 20 °C 3: sodium tetrahydroborate; water / ethanol / 1 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: copper(II) sulfate / Acidic conditions 2: acetic anhydride; PDC View Scheme |
D-glucofuranose
Diacetone D-glucose
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sulfuric acid 2: phosgene; triethylamine / dichloromethane / 1.5 h / -78 - 20 °C 3: sodium tetrahydroborate; ethanol / water / 1 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: zinc(II) chloride; phosphoric acid / 15 - 30 °C / Large scale 2: potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium hydrogencarbonate / water; ethyl acetate / 0 - 35 °C 3: sodium tetrahydroborate / water / 10 - 15 °C View Scheme |
Conditions | Yield |
---|---|
With water; acetic acid at 20℃; for 8h; regioselective reaction; | 100% |
Stage #1: Diacetone D-glucose With carbon tetrabromide In methanol for 0.5h; Irradiation; Stage #2: In methanol at 20℃; for 14.5h; | 90% |
With silica supported polyphosphoric acid In acetonitrile at 55℃; for 0.5h; | 82% |
trifluoromethylsulfonic anhydride
Diacetone D-glucose
1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -30℃; for 0.75h; | 100% |
With pyridine at 0 - 20℃; Inert atmosphere; | 95% |
With pyridine at 0 - 20℃; for 3.5h; | 92% |
5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
Diacetone D-glucose
(1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-O-yl) 3-oxobutanoate
Conditions | Yield |
---|---|
In toluene for 8h; Heating; | 100% |
benzyl bromide
Diacetone D-glucose
1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 8h; | 100% |
Stage #1: Diacetone D-glucose With sodium hydride In acetonitrile; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: benzyl bromide In methanol; acetonitrile; mineral oil at 0℃; for 4.5h; | 90% |
With sodium hydride | 60% |
benzoyl cyanide
Diacetone D-glucose
(+)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl benzoate
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 0℃; | 100% |
With triethylamine In acetonitrile at 20℃; for 15h; |
tert-butylchlorodiphenylsilane
Diacetone D-glucose
tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 18h; | 99% |
binaphthol chlorophosphite
Diacetone D-glucose
Conditions | Yield |
---|---|
With triethylamine In toluene for 16h; | 99% |
With triethylamine In toluene for 16h; | 98% |
acetic anhydride
Diacetone D-glucose
3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
Conditions | Yield |
---|---|
With iron(III) sulfate at 20℃; for 6h; | 99% |
With pyridine at 20℃; | |
With pyridine |
Conditions | Yield |
---|---|
With triethylamine In toluene at 20℃; for 72h; | 99% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 2h; | 99% |
2-bromomethylnaphthyl bromide
Diacetone D-glucose
3-O-(2-naphthylmethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0℃; | 99% |
With sodium hydride In N,N-dimethyl-formamide for 1.16667h; Cooling with ice; | 99% |
With sodium hydride In N,N-dimethyl-formamide for 1h; Cooling with ice; | 99% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide for 1h; Cooling with ice; | 99% |
Conditions | Yield |
---|---|
With dmap; triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h; | 98% |
Diacetone D-glucose
(4-tert-Butyl-phenyl)-methanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 24h; | 97% |
Conditions | Yield |
---|---|
With triethylamine In toluene at 20℃; for 2h; | 97% |
hexadecylamine
2,4-bis(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide
Diacetone D-glucose
Conditions | Yield |
---|---|
Stage #1: 2,4-bis(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide; Diacetone D-glucose In benzene at 20℃; for 1h; Inert atmosphere; Stage #2: hexadecylamine In benzene at 20℃; for 1h; Inert atmosphere; | 97% |
butyryl chloride
Diacetone D-glucose
3-O-butanoyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
Conditions | Yield |
---|---|
With triethylamine In toluene at 20℃; for 2h; | 96% |
(Z)-2-methyl-2-butenoic anhydride
Diacetone D-glucose
3-angeloyl-1,2:5,6-O-isopropylidene-allofuranose
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; for 0.5h; | 96% |
Diacetone D-glucose
(3S)-3-chloro-3-deoxy-1,2:5,6-di-O-isoproplylidene-α-D-allofuranose
Conditions | Yield |
---|---|
Stage #1: Diacetone D-glucose With sulfuryl dichloride In dichloromethane at -5 - 0℃; for 0.666667h; Inert atmosphere; Stage #2: With 1,2,3-Benzotriazole In dichloromethane at 20℃; for 6.5h; Inert atmosphere; | 96% |
trifluoromethylsulfonic anhydride
Diacetone D-glucose
1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose
Conditions | Yield |
---|---|
Stage #1: Diacetone D-glucose With pyridine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 0℃; Inert atmosphere; | 96% |
tert-butyldimethylsilyl chloride
Diacetone D-glucose
3-O-[(tert-butyl)dimethylsilyl]-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 18h; | 95% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere; | 94% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; silylation; |
benzoyl chloride
Diacetone D-glucose
(+)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl benzoate
Conditions | Yield |
---|---|
In pyridine at 20℃; for 6h; Acylation; | 95% |
With pyridine at 20℃; for 20h; | 90% |
With pyridine at 0 - 20℃; Inert atmosphere; | 90% |
With pyridine In dichloromethane at 0℃; for 1h; | |
In pyridine |
p-toluenesulfonyl chloride
Diacetone D-glucose
1,2,5,6-di-O-isopropylidene-3-O-(p-toluenesulfonyl)-α-D-allofuranose
Conditions | Yield |
---|---|
With pyridine at 20℃; Tosylation; | 95% |
With pyridine | 91.6% |
With pyridine at 0 - 20℃; | 66% |
With pyridine; dmap at 20℃; for 48h; | 57% |
With pyridine; dmap In dichloromethane at 0 - 20℃; for 12h; Product distribution / selectivity; |
Diacetone D-glucose
3-deoxy-1,2;5,6-di-O-isopropylidene-3-fluoro-α-D-glucofuranose
Conditions | Yield |
---|---|
With pyridine In dichloromethane; toluene at -78 - 40℃; for 168h; | 95% |
With (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane; toluene at -78 - 40℃; for 168h; | 95% |
With potassium fluoride; 1,3-bis(2,6-diisopropylphenyl)-2,2-difluoro-2,3-dihydro-1h-imidazole; N-ethyl-N,N-diisopropylamine In toluene at 80℃; for 16h; Inert atmosphere; | 83% |
2-chloroethyl methyl ether
Diacetone D-glucose
1,2:5,6-di-O-isopropyliden-3-O-(2-methoxyethyl)-α-D-allofuranose
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 55℃; for 7.5h; | 95% |
allyl bromide
Diacetone D-glucose
1,2:5,6-di-O-isopropylidene-3-O-allyl-α-D-allofuranose
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 25℃; for 2h; | 95% |
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In dichloromethane; water at 23℃; for 5h; | 92% |
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 3h; | |
With tetra-(n-butyl)ammonium iodide; sodium hydroxide In dichloromethane; water at 23℃; for 5h; |
isopropyl 2-bromoacetate
Diacetone D-glucose
Conditions | Yield |
---|---|
With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine In tetrahydrofuran at 0 - 20℃; for 48h; | 95% |
2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate
Diacetone D-glucose
2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 4h; Molecular sieve; Inert atmosphere; | 94% |
1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose (2595-05-3) is called for 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranoside ; Diacetone-alpha-D-all ; 5-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-D][1,3]dioxol-6-ol ; Diisopropylideneallofuranose ; Diacetoneglucose ; ZINC04262105 ; CID7157054 ,and so on. 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose (2595-05-3) is white solid.
IUPAC Name: (3aR,5S,6R,6aR)-5-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
CAS: 2595-05-3
Molecular Formula: C12H20O6
Molecular Weight: 260.28
Molecular structure:
Melting point: 73-76 °C(lit.)
Storage temp.: 2-8°C
H bond acceptors: 6
H bond donors: 1
Freely Rotating Bonds: 2
Index of Refraction: 1.483
Molar Refractivity: 61.24 cm3
Molar Volume: 214.3 cm3
Polarizability: 24.28 10-24cm3
Surface Tension: 43.6 dyne/cm
Density: 1.214 g/cm3
Flash Point: 173.2 °C
Enthalpy of Vaporization: 70.46 kJ/mol
Boiling Point: 362.8 °C at 760 mmHg
Vapour Pressure: 9.94E-07 mmHg at 25°C
1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose (2595-05-3) is commonly used as chemical reagent.
Hazard Codes: Xi
Risk Statements: 36/37/38 (36/37/38: Irritating to eyes, respiratory system and skin)
Safety Statements: 22-24/25-36/37-26 (22: Do not breathe dust 24/25: Avoid contact with skin and eyes 36/37: Wear suitable protective clothing and gloves 26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice)
WGK Germany: 3
F: 21
Removal in wastewater treatment of 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose (2595-05-3) can be stated as follows:
Total removal:2.71 percent
Total biodegradation:0.10 percent
Total sludge adsorption:2.62 percent
Total to Air:0.00 percent
(using 10000 hr Bio P,A,S)
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